(1S,2R,8S,10S,11S,13S,14S,15S,17S)-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-13-(2H3)methyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 169062
• Molecular Formular: C22H29FO4
• Molecular Mass: 376.4616632
• Monoisotopic Mass: 376.20498763
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1C[C@@H]([C@@H]2C(=O)CO)C)C)O)F)C
• Canonical SMILES: OCC(=O)[C@H]1[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C22H29FO4/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-21(15,2)20(13)17(26)9-22(14,3)19(11)18(27)10-24/h4-5,7,11,13-14,16-17,19-20,24,26H,6,8-10H2,1-3H3/t11-,13-,14-,16-,17-,19+,20+,21-,22-/m0/s1
• InChIKey: GAKMQHDJQHZUTJ-VSZBBTLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10S,11S,13S,14S,15S,17S)-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-13-(^2H₃)methyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,8S,10S,11S,13S,14S,15S,17S)-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-13-(^2H₃)methyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: 6α,11β,16α)-6-Fluoro-11,21-dihydroxy-16-(methyl-d3)pregna-1,4-diene-3,20-dione; 16α-(Methyl-d3)-6α-fluoro-Δ1,4-pregnadien-11β,21-diol-3,20-dione; 6α-Fluoro-16α-(methyl-d3)-Δ1-corticosterone; Flucortolone-d3; Fluocortolon-d3; SH 742-d3; Fluocortolone-d3

Database IDs

• PubChem SID: 162263194
• PubChem CID: 71316792

CALCULATED PROPERTIES

• Acid pKa: 13.842936
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.9677155
• LogD (pH = 7.4): 1.9677147
• Log P: 1.9677149
• Molar Refractivity: 101.4653 cm^3
• Polarizability: 38.960613 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F500502

Labelled Fluocortolone (F500500). Glucocorticoid.

REFERENCES

• Breuer, et al.: Arzneim.-Forsch., 15, 50 (1965)
• Domenico, et al.: Arzneim.-Forsch., 15, 46 (1965)
• Gerhards, et al.: Acta Endocrinol., 68, 98 (1965)